Ethanol → HCID 86734510, compound

HRID 436652Notes

Reaction equation

HRID 436652 reaction equation
[CH2:1]([NH:22][C:23](=[O:35])[C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)[CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1.C(O)C.[H][H]>N1C=CC=CC=1>[CH2:1]([NH:22][C:23](=[O:35])[C:24]1[CH:25]=[CH:26][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:28][CH:29]=1)[CH2:2]/[CH:3]=[CH:4]\[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]([F:19])([F:20])[F:18])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 21452973HCID 21452973, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86734510HCID 86734510, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution containing 9.86 g. of N,N'-(3-heptyne-1,7-diyl)bis(4-trifluoromethoxybenzamide) in 110 ml. of ethanol and 5.0 ml. of pyridine was hydrogenated in a Parr shaker using 1.0 g. of palladium-on-barium sulfate using an initial pressure of hydrogen of 35.5 psi and taking about 40 minutes. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated in vacuo to remove the sulfate. The white crystalline solid residue was recrystallized from carbon tetrachloride using a small quantity of methanol to yield, as a white microcrystalline powder after drying in vacuo at 60° C. for about 50 hours, 7.6 g. of N,N'-(cis-3-heptene-1,7-diyl)bis(4-trifluoromethoxybenzamide), m.p. 111°-113° C.

Workup

  1. additionA solution containing 9.86 g
  2. filtrationThe reaction mixture was filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto remove the sulfate
  6. customThe white crystalline solid residue was recrystallized from carbon tetrachloride using a small quantity of methanol
  7. customto yield, as a white microcrystalline powder
  8. customafter drying in vacuo at 60° C. for about 50 hours

Sources & evidence

ORD record
ord-3b62b9aec8bf4f949f00d4f809a87808
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

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